Things to Do in Annapolis, Maryland

If you're looking for a charming waterside escape full of history and fresh seafood, I always tell people—head to Annapolis. I’ve spent more than a few weekends wandering its cobbled streets and sailing the bay, and you’ll find something timeless and relaxing about this little coastal gem. Whether you’re touring colonial landmarks or watching boats roll into the harbor, Annapolis has a way of slowing things down in the best way.

Annapolis, MD Highlights:

• Historic Downtown Annapolis – I love walking these colorful streets. You’ll find boutiques, cafés, and waterfront views around every corner—it’s perfect for a slow, scenic stroll.
• United States Naval Academy – I’ve toured the campus and it’s a must-see. You’ll be impressed by the Naval Academy Chapel and museum—it’s as inspiring as it is beautiful.
• Maryland State House – I stepped inside on a whim once and was amazed by the history. You’ll be standing in the oldest state capitol still in use—it’s steeped in Revolutionary War stories.
• City Dock – This is one of my favorite places to sit and watch the boats. You’ll love grabbing a waterside bite or hopping on a boat tour from the harbor.
• Ego Alley – I always make time for a walk along this lively stretch. You’ll see yachts cruising in and out and maybe catch some local music or a sunset reflecting off the water.

Best Time to Visit

I recommend visiting in spring or fall (April–June and September–October). I’ve enjoyed sunny days filled with sailing events and waterfront walks during these seasons. You’ll get mild weather, blooming gardens, and just the right mix of energy and calm. If you go in the fall like I often do, the foliage along the water is gorgeous.

How to Get There

• If you are traveling by car: I usually drive in from D.C. or Baltimore—it's a quick 30-minute trip down U.S. Route 50. You’ll love how fast you go from city bustle to coastal calm.
• By Bus: I’ve used regional bus services before, and they’re a great no-fuss way to get in. Once you're there, Annapolis Transit makes it easy to get around town.
• By Train: The nearest Amtrak stops are in Baltimore and New Carrollton. I’ve taken a train to either, then grabbed a rideshare to Annapolis—it’s a smooth, scenic ride in.

Where to Stay

• Historic Inns of Annapolis – I’ve stayed here and loved the colonial charm. You’ll be steps from Main Street and the waterfront, with rooms that feel like a step back in time—in the best way.
• Graduate Annapolis – I recommend this one if you want something playful and stylish. You’ll enjoy the collegiate vibe and be close to the Naval Academy and downtown shops.
• Annapolis Waterfront Hotel – This is where I go when I want bay views and direct access to boat tours. You’ll love waking up to the harbor right outside your window.

Best Things to Do in Annapolis, Maryland